The Tale of Jack Despair
by DragonMaster77
Summary: Nightwing is obsessed with finding out how Mono came to exist that he can't sleep. With Twilight's help he views the past life of Jack Despair seeing how the alicorn lived and how he became the spirit of despair.
1. Prologue: A Sleepless Night

My first offical My Little Pony story. Here is the start where we meet the one wanting to know more about a dangerous enemy to Equestria.

Disclaimer: I only own Nightwing, Ace and Mono. I do not own My Little Pony

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 **Prologue: A Sleepless Night**

It was on the dark streets of an Equestrian town far from Canterlot and Ponyville known as Haydon. No one was out on the dark streets.

Well there was one pony; he was a black Pegasus with a blue mane and tail, wearing a blue suit with an old green fedora hat. His name was Nightwing a detective who was from Manehatten but had moved to Ponyville.

He had relatives in Haydon but that wasn't why he was here, in fact he didn't know why he was here till he heard a laugh. One he knew well. He turned to look behind him to see a dark shadow approach.

This shadow had the shape of an alicorn and red eyes with an evil toothy smile. Soon the shadow's dissipate to reveal a robotic alicorn pony that was back and white with red soulless eyes but the same smile.

"Mono! Or have you gone back to using Jack you insane spirit!" Nightwing said angry at the being

"Insane? Ohhhhh that hurts…really it does. Oh the despair I feel knowing that's how you feel about me" Mono said feigning sadness but laughs and said "It feels very good"

"I hate that you enjoy that but I expect no less from the spirt of despair" Nightwing said staying on guard.

"Yeah but you and I are connected since I tried to get you as a host and left a part of me in you, but now…I want that back" Mono said grinning and soon his arts separate as he grows to the size of Celestia and it shows his metal body is more armour for the shadowy being and clawed tendril move towards Nightwing.

The Pegasus flies up and tries to get away but is soon grabbed and gets dragged back towards the alicorn being who laughs and said "I do hope you feel despair to you last moments of life as I'm sure it will be good I remember you like that." He then laughs more.

Everything goes dark and Nightwing screams and wakes up and he looks around panicked. He was in an office sitting at a desk…his desk. He sighs and places his hooves on his face and rubs it and said "It was all a dream…." He felt a third thing touch his face and looks to see a shadowy clawed hoof touching him which was coming from his own body

"Will you get off me?!" Nightwing cried to the shadowy claw which retracts back into him. Ever since he was once possessed by Mono when he was Jack and got him out he gained the clawed hoof, so far he only knows how to use it to protect himself nothing else but it also serves a reminder that now him and the spirit of despair were connected.

An eagle flies in and looks at Nightwing. The eagle was Nightwing's pet and the pony smiled tired but said "I'm fine Ace, just another nightmare…" he yawns and looks at the letter he was reading before he fell asleep.

Nightwing has become obsessed over finding out who Mono was before the whole shadow spirt, as he learned there was an alicorn named Jack Despair in Haydon many years ago, but the letter from his cousin said no records on the pony seem to exists. Naturally this need to know has caused him to suffer nightmares preventing him from sleeping.

"No files of him exists…there either lost or all traces of Jack are gone but…how am I going to know" Nightwing said rubbing his head and hears a screech.

He looks to Ace who draws on a board a tree castle with a alicorn on it and Nightwing got it "Twilight of course…maybe…maybe she knows a spell to allow us to see into the past and know the truth…I hope so at least good idea Ace." Nightwing said and yawned "We'll visit her in the morning and hope she can help but…but sleep first or at least…I'll try to sleep" He said going up to his room to fall asleep

Ace looks at his owner with concern he hopes Twilight can help because this obsession, it may destroy him mentally with the nightmares.

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With that the prologue has eneded next time Nightwing will meet up with Twilight who will provide a window into the past so they can see how Mono then Jack Despair was in the past as a full alicorn.

Please Read, Review and No flames thank you


	2. Chapter 1: Window into the Past

Here we go the the beginning where we start to know Jack's life with the aid of Twilight and a spell. Also in advance first time I used Spike so sorry if I botched it.

Disclaimer: I only own Nightwing, Ace and Jack Despair.

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 **Chapter 1: Window into the Past**

The next morning Nightwing was walking through Ponyville with Ace riding on his back. He yawns he once again suffered a nightmare but he didn't let it distraught him.

He smiles and waves to several of the town's citizens who wave to him. Since moving her Nightwing has witnessed many events Twilight becoming an alicorn, the attack of the plunder vines, the rise of the friendship castle, just to name a few.

Speaking of the latter Nightwing could see it up ahead and smiles. He trotted to the front door and knocks on the door. He yawns as the door opens and Spike answers the door.

"Oh hey detective Nightwing, what brings you here so early?" Spike asked curious as to why the detective pony was here.

"Morning Spike so to be a bother but I need to see Twilight on an urgent matter" Nightwing said a little a tired but managed to stay standing.

"Sounds more like you can use a bed but come in and I'll get her for you" Spike said noticing how tired Nightwing sounded but allows him and he goes to get Twilight.

Nightwing looks around he could never get used to the place. Soon he hears trotting and turns to see the princess of friendship herself

"Spike says you needed to see me, he also mentioned it was serious as you look like you haven't slept for a while and I can see" Twilight said voicing her concern.

"Yeah…I'll be fine but that is why I'm here…I have become obsessed with a personal case about a being of darkness and evil." Nightwing explained "He's named Monopony but he was once known as Jack the Despairer and It's been keeping me up trying to learn who he was."

"So why is this important to you? Is it related to that dark arm you can summon? And why come to me?" Twilight asked curious about it

"Well…Ace why don't you go and hang out with Owowiscious while I talk with Twilight" Nightwing said, Ace nods and flies off. "Anyway to answer your questions in order, I rather not get into it yet, yes it is and the reason I'm here is I learned in the past in Haydon there was an alicorn named Jack Despair but there is no record of him in Haydon."

"So you came to me to see if there was anything I can do to help?" Twilight asked him and Nightwing nods to her. "Well…I haven't got any books from Haydon but I do know a spell that can help"

"Really? That would really help" Nightwing said smiling while Spike came in with some coffee for the two.

"Thanks Spike, can you watch Owowiscious and Ace, I call you if I need anything" Twilight said and Spike nods leaving the room. Twilight then closes her eyes and her horn courses with magic and suddenly a mirror appears hovering in front of them.

"It's….a mirror? Can you explain as I don't understand" Nightwing asked confused before sipping the coffee

"It's a time mirror mainly you ask it what you want and it will shows you the past of what was asked." Twilight explained "Give it a try."

Nightwing goes to the mirror and said looking into it and said "Mirror…show me how Jack Despair came to be the spirit of Despair and his life before."

The Mirror flashes and the reflection changes showing Haydon much more older and the image was off Buckinghoof Palace, It vanished and the two ponies notice there actually at the area but the pony guards walk through them.

"Let me guess all this is a magical illusion and we're not really here" Nightwing asked and Twilight nods.

Soon a very fancy carriage stops and out steps a black and white alicorn pony with fancy hair and red eyes dressed in a suit with a top hat. Nightwing instantly despite seeing him like this for the first time knew who it was

"Not presenting Lord Jack Despair head of Haydon Science and Development" The pony announcer called out as Jack made his way into the palace.

"Lord….should have guessed" Nightwing said glaring at Jack made his way inside

"Nightwing relax I'm sure after this I may see the kind of enemy this pony came to be for you" Twilight said.

Nightwing sighs and nods' understanding now was the time to listen and watch the events unfold. The scene soon begins to change to show the inside of the palace.

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Well Nightwing didn't expect that but next time we'll see if Jack was respected or always a monster.

Please Read, Review and No Flames.


	3. Chapter 2: Jack's Experiments

Here is the next chapter.

Disclamer: I do not own Twilight or MLP only my characters

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 **Chapter 2: Jack's Experiments**

As the two ponies enter the scene of the party they see Jack talking with other guests. He seemed to act like a proper gentlecolt but Nightwing didn't trust him

"So Sir Jack, how goes you experiments, what were they again?" an old rich pony asked Jack

"Now dear sir, there's a reason my research is tagged classified, meaning I can't freely tell anypony what it is but I can say we're near a breakthrough." Jack told the pony politely.

"I must say Jack, you are always such a charming man to meet" A fancy mare said to him

"My lady you flatter me" Jack said charmed but then adds "I am afraid I cannot stay for long."

"Mr. Despair" a voice called and Jack turned to see a pony in a suit and a top hat holding a pipe "Leaving so soon?"

"Mr. Holmes, I'm surprised to see you're here" Jack said surprised a bit

"Oh….I can't believe it! It's Sherehoof Holmes!" Nightwing said shocked and happy to see his idal here.

"Well….who knew we meet him during this trip back" Twilight said equally surprised.

"The queen invited me to this along with my colleague Dr. Hoofston. Anyway I was hopeing you can discuss with me some disappereance of some mares who a few days later end up being found dead in the streets where you live which is Haychapel." Sherehoof said serious.

This caught Jack off guard and he said "Well…I'm afraid now isn't the best time, my research is in the most important stage, sometime next week?"

"Very well" Sherehoof said taking note on how Jack acted.

Jack nods and excuses himself as he leaves the party. Much to the disappointment of some mares. However Sherehoof watched him suspiciously, he knew Jack was hiding something over how he reacted to the topic he wanted to discuss.

The scene changed for the watching ponies to the streets of HayChapel it was dark and slightly foggy and hardly anypony out.

"HayChapel, the area where the victims of some strange deaths of mares occurred." Nightwing said looking around

"How strange?" Twilight asked concerned

"It was like they died from despair." Nightwing said shuddering and hearing that made Twilight shudder as well.

Soon Jack emerged from the fog and enters his home where the watchers followed. Jack sighed with relief but said to himself "That foolish great detective is getting close, my machine needs to be ready if I'm to make my move"

He then pulls out a book from his bookshelf and a secret passage open up and he heads down the stairs. As he goes down the sound of a female screaming.

Once at the bottom we're now in what looks like a dark temple dungeon mixed with a lab. There was a big steam powered machine with an axe attached to it. I was firing a black beam at a mare strapped to the temple.

There were many ponies in robes working acting like the pony in distress was normal. Which it was as Nightwing figured out "I already knew Jack was the cause of those deaths as he told me."

"This…this is so disturbing…" Twilight said shocked and horrified as all this.

Nightwing pats Twilight on the back reassuring her. He said "It'll be okay Twilight…Jack got what was coming to him which we'll see."

Jack approaches a cloaked pony on the controls of the machine and asked serious "Iron Works, how goes the experiments with the Despair axe?"

The pony removes hood showing he was an brown black maned Earth pony with an eye patch "So far so good. We up to 50% power and she's still alive and the machine as broken, we are about to go to 60%"

"Not good enough, go to a hundred now" Jack ordered in an 'I'm serious voice'

"But sir…" Iron Works began but seeing the look sighs and turns the dial to hundred increasing the power. The mare screams louder but soon the machine sparks and fails. Iron Works grows "Darn it, overheated again!" He goes over to the machine and examines it.

"How is the subject?" Jack asked uncaring. One pony checks and shakes his head "Dead…what a shame."

"Well the damage wasn't too bad" Iron Works said fixing it "But this is the last time I can repair it, I'm shipping out soon to a new land to expand my business."

"Such a shame Iron Works, you've been loyal" Jack said to him and adds "Before you go despose of the body, but somewhere over then Haychapel that should throw off Sherehoof for a while."

"Yes sir, hey Talltale!" Iron Works calls out getting the attention of a green and red maned unicorn by surprise "Come help me move this body. We need to put her somewhere"

"S-Sure…" Talltale said nervous and the two ponies remove the mare and dump her into Iron Work's cart and the two pull it out of the secret exit.

Nightwing watching said "Let's follow them for a while."

"Why?" Twilight asked curious in Nightwing's reasoning "Think there up to something."

"Yeah…I recall hearing from Mono that an Iron Works was one pony who caused his curse. If that pony is the same one here I need to find out if he is the cause" Nightwing explained to Twilight

"Alright, let's follow them" Twilight said as she uses the magic to transfer this to the magic mirror.

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Well Jack truely is a monster. But Nightwing suspect two of his helpers may have had a hand in his downfall. Next time we see if he's right.

Please Read, Review and No flames please.


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